The demand for chiral organic molecules for medicinal and theoretical applications, and novel materials, continues to increase with significant acceleration. However, the development of the means to produce these agents by safe and environmentally sound methods has not kept pace. We propose to introduce novel, aqueous, and telescoping chiral auxiliary technologies for the preparation of chiral materials. The proposed technology constitutes a new paradigm for auxiliary technology that obviates the need for discreet steps for auxiliary installation and removal. Moreover, the technology may eliminate the requirement for the processing of chemical intermediates that are typical of multi-step sequences. These proposed studies build on the solid conceptual foundation of chirality transfer in conventional, well-characterized, auxiliary-mediated asymmetric processes. Our proposed auxiliary is the first to be designed specifically for aqueous application and is the first auxiliary system designed to incorporate a telescoping capability to these transformations. These attributes will significantly reduce the chemical wastes associated with auxiliary-mediated, multi-step sequences that have reduced the attractiveness and application of auxiliary technology. As described below, we have developed a proof-of-concept system for the proposed technology, however, significant work remains to be completed. The specific issues to be investigated under this project include: the origin and amplification of chirality transfer, origin and reduction of minor products and the breadth of potential applications of this technology. As a consequence of the proposed studies, we will enable the production of selected chiral materials via safer and substantially more environmentally friendly chemical methods. In addition, we will have firmly established the concept that chiral organic products can be generated under aqueous conditions and with significantly fewer overall synthetic steps. Our laboratory has made significant contributions to green applications and is ideally poised to pursue these studies.